Soul Mating

By Laura Milligan

Younger men have undoubtedly been dating older women for decades, but only in the last several years has there been a more public display of this type of cross generational affection. But what is it that older women find attractive in younger men, and vice versa? Find that out and more in this ultimate guide to pursuing and dating cougars.

Before You Start

There are definitely some things you should consider before going after a cougar, from knowing how to keep older women interested and engaged to bracing yourself for disapproving friends and family.

1. Know your goals: Do you want a fling or a serious relationship that will leave you set for life financially? Narrowing down your goals will help you zero in on the right kind of cougar.
2. Do your research: The most sought after cougars are smart and sophisticated, so make sure you have enough to talk about.
3. Know how to please a woman: Older women who are dating younger men expect a lot of attention and enthusiasm in the sack, so don’t disappoint.
4. Be ready to be available: Don’t waste your time if you’re going to play hard to get. You’re the boy toy in this scenario, so be ready to go out on dates whenever she wants.
5. Shower compliments on her whenever appropriate: Make your cougar feel attractive and young again by showing her off to friends and showering her with compliments.
6. It’s not going to be all about you: Sure, you’re there to make her feel special and sexy in front of her friends, but the whole game is more about fulfilling her needs than yours.
7. Understand the social stigma: If you’re not planning on getting serious, you may want to keep your relationship on the DL, because there’s still a social stigma attached to cross-generational dating.
8. Use a condom: If your cougar is past menopause, you still need to use a condom to protect against STDs.
9. Beware of legal battles: Understand that your cougar’s children might call a lawyer if you suddenly replace them in their mother’s will.
10. Get defensive: If you’re legitimately looking for a long term relationship with an older woman, be careful of those cougars who just want a fling with a younger man.

Dating Sites

Find older women who aren’t shy about their affinity for younger men on these online dating web sites.

11. goCougar: A free sign up gets you in to rate pictures, see videos and chat online with cougars.
12. Date a Cougar: Check out this dating site to find cougars all over the country.
13. DateOlderWomen.com: Send and receive messages, maintain a dating profile and search for older women here.
14. Cougared: Join this dating site to view thousands of profiles all over the world. You can also keep a blog and upload photos.
15. Matchmaker: This site is open to cougar girls, men, gay individuals and lesbians.
16. Match.com: Check out this page devoted to cougar dating.
17. Cougar Women on Dating Sites: The blog Hot and Trendy explores the presence of older women on dating sites.
18. ToyBoyClub: If you’re in the UK, visit this online dating site "where mature ladies meet younger men."
19. CougarDate.com: While the dating service on this site is currently under reconstruction, you can still read all about cougars and get tips for snagging one yourself.
20. CougarsLair: This very simple dating site has a small dating pool, increasing your chances of getting noticed.

Understanding the Cougar

Gain some insight from these articles in order to prepare yourself for the seduction and your relationship.

21. MainStreet Cougar Dating Money Rules: Get some insight into the needs and wants of older women in this article, which claims that "it’s not money that cougars are after."
22. Why do older women date younger men?: This article points out different reasons why cougars have flings with younger men, including the ability to be in charge and call all the shots.
23. Cougars and Their Cubs: Read an interview with a lifelong cougar to discover some of the appeal of dating younger men.
24. Older Woman, Younger Man Relationships: MSNBC’s 2003 article takes a look at what was then considered a "pioneering" cougar moment.
25. Dating definition: cougar: Read this silly but somewhat accurate definition of a cougar.
26. What Older Women Want in a Man: This tongue-in-cheek checklist will give you an idea of whether or not you’ll make the cut.
27. The Secret Lives of Single Women: Find out how single women really feel about their independence.
28. How to Date a Divorced Woman: Many cougars looking for younger men are divorced, so understand what you’re getting into by reading this article.
29. Pursuing Successful Women: Learn how to snag a successful, independent woman here.
30. What to Do When She’s More Successful: If you become threatened by your cougar’s superior success and status, read this article to help calm you down.

Networks and Opportunities

This list includes several more networking opportunities and places that will connect you to cougars.

31. UrbanCougar: Check out the featured UrbanCougar of the month, take advantage of the dating services, and even purchase t-shirts and gag gifts that express your enthusiasm for older women.
32. Singlescene cougar discussion: Read interviews with cougars and participate in an online discussion to find out what older women expect out of their dates.
33. The Real Cougar Woman: Check out this site to read about what cougars want out of their relationships and lifestyles.
34. Woman Attract: This blog and dating tips site features categories on seduction and dating news.
35. Boomer Dating TV: Consider joining this dating service, which combines video dating and online dating.
36. Cougar Dating Reality Show TV Land 2009: Tune in or send in your application for this reality show that pairs a cougar with a much younger man.
37. Real Cougar Club: If you’re really desperate or sneaky, you can ask one of your older woman friends to join this network, and then introduce you to all of her new friends.
38. Meet Cougar Women at Hot or Not: This dating rating site has a page just for cougars and the guys who love them.
39. Create an ad: If you don’t feel like creating an online profile, write an ad that explains your situation and your desire to meet a a mature woman.
40. Go to fundraisers and charity events: If you’re set on meeting a benefactress, head to high-profile fundraisers and parties.
41. Ageless Love: Find support for "age gap relationships" here.

Dealing with the Family

Along the way, you may encounter children who are older than you are, ex-husbands and legal headaches. Figure out how to navigate the family situation here.

42. Anna Nicole Smith vs. E. Pierce Marshall: Who could forget the legal battle that ensued between Anna Nicole and her late husband’s son? Make sure this doesn’t happen to you.
43. Stay low-key: You may be the same age as your girlfriend’s kids, but that doesn’t mean they want to hang out with you.
44. Understand their suspicions: If a rich woman suddenly starts dating a younger man, her family is going to suspect you of gold digging.
45. Follow her lead: Only attend family events when your cougar specifically invites you. She may only want you for the sex, so don’t try to invade her family life too.
46. Don’t talk about money: The more you talk about money, vacations, and elaborate expense accounts, the more her family will mistrust your intentions.

Dating Psychology

Discover why older women are attracted to younger guys like you in these articles.

47. What do guys in their 20s want with women in their 40s?: This blog considers cougar relationships from the other end and decodes why younger men even want to be with older women.
48. What Women Want is a Younger Man: This article discusses the evaporation of sugar daddies and the new popularity of sugar mamas.
49. Cougars, Dating and Double Standards: This discussion between five women considers questions like "is an older women dating a younger guy a big deal?" and "Cougar: celebratory or patronizing?"
50. Older Woman Seeking Boy Toy: DatingThoughts.com’s guide categorizes women who date younger men as "pumas," "cougars," and "jaguars." Read all about it here.
51. Lifestyles, Dating and Romance: A Study of Midlife Singles: Learn the statistics of midlife single women, and you’ll be more prepared to date one.
52. Don’t Call Me a Cougar: Before coming right out and joking to your girlfriend that she’s a cougar, read this article.
53. Australian Online Dating Site Tells Why So Many Men are Attracted to Older Women: Learn why financial security and submissive personalities are two of the top reasons younger men turn to older women.
54. Younger Men, Better Sex?: CBS’ investigation discovers that younger men and older women are experiencing similar sexual peaks.
55. Younger Women Who Desire Older Women: This blogger has generated a list of testimonials from younger men who have experience with older women.
56. Are More Older Women With Younger Men?: Find out why "cougars" are more common and not as taboo.

Articles and Guides

For some guidance and insight into dating cougars, turn to these articles.

57. Confessions of a Cougar: Learn about "the pros and cons of cougar-hood" and the reasons why women date younger men.
58. Welcome to Cougartown: Use this calculation tool to figure out if you’re in fact dating a cougar.
59. Dating Older Women: Read this article, written by someone who has experience with "quite a few predatory felines."
60. Dating Older Women: Younger men will find tips for making it work with an older women here.
61. Tips from Cougar Valley: Learn the proper ways to approach an older woman online.

Celebrity Inspiration

If you’ve always wanted to date an older woman but wanted a little extra motivation to get started, check out these successful cougar couples.

62. Demi and Ashton: These two practically started the cougar trend when they got together several years ago and were the subject of a lot of praise and cradle robber jokes.
63. Halle Berry and Gabrielle Aubry: Berry is nine years older than her model boyfriend, Gabriel Aubry, but the age difference hasn’t stopped the two from procreating.
64. Madonna and Guy Richie: The ultimate in successful career women and sexual liberation, Madonna is 10 years older than husband Guy Ritchie.
65. Samantha and Smith: One of Sex and the City’s hottest couples, Samantha Jones and Smith Jared proved an inspiration to older women everywhere.
66. Kim Cattrall and Alan Wyse: Taking a cue from her onscreen character, Kim Cattrall of Sex and the City fame has been dating chef Alan Wyse for a few years, despite a 23-year age gap.

Sex and Romance Tips

Wooing and dating an older woman is very different from hooking up with a college girl. Learn more sophisticated sex and romance tips here.

67. Sexuality at Midlife and Beyond: 2004 Update of Attitudes and Behaviors: This report explores the sexuality of a broad range of midlife individuals.
68. Remember your manners: Chances are your cougar has been around the block a few times and has experienced the bad and the good. Make sure to hold the door open for her and be polite.
69. Pink Parts - Female Sexual Anatomy: It can’t hurt to get a little crash course in the female anatomy before trying to please your cougar. She’s probably in the prime of her sexuality and is expecting you to satisfy her.
70. Older Women Talk About Sex: Find out how older women view sex and their own sexual desires.
71. How to Seduce an Older Woman: Get tips on closing the deal here.
72. Avoid cheesy pick-up lines: You know she’s heard them all already anyway.
73. Be attentive: Ask about her life, job, etc., but always remember to follow her lead. If she stays tight-lipped about a certain subject, don’t bother to bring it up again.
74. Hello, Mrs. Robinson: Tips for seducing your cougar include "be your own man" and "don’t move too fast."
75. Top 10 Sex Tips for the Older Woman: Review these tips before jumping in the sack with your cougar.

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